60282-87-3
60282-87-3
Chemical Structure
Gestodene
Synonym(s): SHB 331; WL 70
- CAS No.: 60282-87-3
- Formula:C21H26O2
- Molecular Weight:310.43
IUPAC Name: (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
InChIKey: SIGSPDASOTUPFS-XUDSTZEESA-N
SMILES: CC[C@@]1([C@]2(O)C#C)[C@](C=C2)([H])[C@@](CCC3=CC4=O)([H])[C@]([C@@]3([H])CC4)([H])CC1
Biological Activity: Gestodene (SHB 331; WL 70) is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis[1][2][3][4][5][6][7][8].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
|
Gestodene | 99.89% | Gestodene (SHB 331; WL 70) is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Gestodene (Standard) | ≥98% | Gestodene (Standard) (SHB 331 (Standard); WL 70 (Standard)) is the analytical standard of Gestodene (HY-B0110). This product is intended for research and analytical applications. Gestodene is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Gestodene-d7 | Gestodene-d7 (SHB 331-d7; WL 70-d7) is the deuterated-labeled Gestodene (HY-B0110). Gestodene is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Gestodene-d6 | Gestodene-d6 (SHB 331-d6; WL 70-d6) is the deuterated-labeled Gestodene (HY-B0110). Gestodene is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Tosagestin | Tosagestin(Org 30659) is a 19-nortestosterone–derived progestagen. Tosagestinsuppresses ovarian function to a level sufficient to inhibit ovulation. Tosagestininhibits cell growth in T47D-S cells. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Levonorgestrel | 99.98% | Levonorgestrel is an orally active inhibitor of progesterone (HY-N0437). Levonorgestrel has anticancer activity and can induce Apoptosis. Levonorgestrel can be used as a contraceptive and in combination with other medications. Levonorgestrel can be used in the study of osteoporosis and uterine leiomyoma. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Norethindrone (Standard) | 99.05% | Norethindrone (Standard) is the analytical standard of Norethindrone. This product is intended for research and analytical applications. Norethindrone is a female progestin approved by FDA for the treatment of endometriosis, uterine bleeding caused by abnormal hormone levels, and secondary amenorrhea. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Norethindrone-13C2 | Norethindrone-13C2 (Norethisterone-13C2) is the 13C labeled Norethindrone (HY-B0554). Norethindrone is a female progestin approved by FDA for the treatment of endometriosis, uterine bleeding caused by abnormal hormone levels, and secondary amenorrhea. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Etonogestrel (Standard) | 99.47% | Etonogestrel (Standard) is the analytical standard of Etonogestrel. This product is intended for research and analytical applications. Etonogestrel (3-Oxodesogestrel), a biologically active metabolite of progestin Desogestrel, binds with high affinity to progesterone receptors and estrogen receptors in the target organs. Etonogestrel induce FKBP51 mRNA and protein expression in cultured human endometrial stromal cells (HESCs). | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Norethindrone acetate | 99.79% | Norethindrone acetate is a female hormone used for the research of endometriosis. Norethindrone acetate is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Norgestrel (Standard) | ≥98% | Norgestrel (Standard) is the analytical standard of Norgestrel. This product is intended for research and analytical applications. Norgestrel is a synthetic analog of progesterone, a compound commonly found in oral contraceptive pill, and a powerful neuroprotective antioxidant, preventing light-induced ROS in photoreceptor cells, and cell death. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
17α-Ethynyl-19-nor-Δ-5(6)-androsten-17β-ol-3-one | 17α-Ethynyl-19-nor-Δ-5(6)-androsten-17β-ol-3-one (delta-5(6)-Norethindrone), an impurity of Norethindrone, is an anabolic agent. Norethindrone is a progestin athat can be used for endometriosis research. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
6,7-Dehydro Norethindrone | 6,7-Dehydro Norethindrone (6,7-Didehydronorethisterone) (Compound 26) is a Norethisterone (HY-B0554) metabolite. 6,7-Dehydro Norethindrone can be produced by the biotransformation of Norethisterone using Rhizopus microsporus PT2906. 6,7-Dehydro Norethindrone induces Apoptosis, binds to p53 and inhibits the degradation of p53. 6,7-Dehydro Norethindrone selectively exhibits antitumor activity against cervical cancer. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
(+)-Norgestrel | (+)-Norgestrel is a progestin used in birth control pills that has reproductive hormone-regulating activity. (+)-Norgestrel also plays an important role in menopausal hormone suppression. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
References
- [1]. Stanczyk FZ, et al. Gestodene: a review of its pharmacology, potency and tolerability in combined contraceptive preparations. Contraception. 2014 Apr;89(4):242-52.
- [2]. Enríquez J, et al. The synthetic progestin, gestodene, affects functional biomarkers in neonatal rat osteoblasts through an estrogen receptor-related mechanism of action. Endocrine research. 2017 Nov;42(4):269-280.
- [3]. Lemus AE, et al. In vitro metabolism of gestodene in target organs: formation of A-ring reduced derivatives with oestrogenic activity. European journal of pharmacology. 2001 Apr 13;417(3):249-56.
- [4]. Jeon H, et al. Gestodene Accelerates Cutaneous Wound Healing via PAR1-Selective Positive Allosteric Modulation. International journal of molecular sciences. 2026 Jun 18;27(12):5502.
- [5]. Park SH, et al. Gestodene, a novel positive allosteric modulator of PAR1, enhances PAR1-mediated human platelet aggregation. Frontiers in pharmacology. 2024;15:1430548.
- [6]. Pech M, et al. Effect of gestodene on the reproduction of zebrafish (Danio rerio). Environmental toxicology and pharmacology. 2026 Aug;125:105070.
- [7]. Schoonen WG, et al. Effects of two classes of progestagens, pregnane and 19-nortestosterone derivatives, on cell growth of human breast tumor cells: II. T47D cell lines. The Journal of steroid biochemistry and molecular biology. 1995 Dec;55(3-4):439-44. [Content Brief]
- [8]. Enríquez J, et al. The potent contraceptive gestodene exerts insulinotropic effects through its a-ring reduced metabolites with intrinsic estrogen-like activity in pancreatic β-cells. Journal of endocrinological investigation. 2023 Jul;46(7):1333-1341.
